A New Copper Acetate-Bis(oxazoline)-Catalyzed, Enantioselective Henry Reaction

David A. Evans, Daniel Seidel, Magnus Rueping, Hon Wai Lam, Jared T. Shaw, C. Wade Downey

Research output: Contribution to journalArticle

433 Citations (Scopus)

Abstract

A highly enantioselective, nitroaldol reaction catalyzed by a chiral Cu(II) bis(oxazoline) complex has been developed. The reaction scope includes both aromatic and aliphatic aldehydes (15 examples) affording products in good yields and enantioselectivities (87-94% ee). An X-ray structure of the catalyst has been provided along with a rationalization of the sense of asymmetric induction.

Original languageEnglish (US)
Pages (from-to)12692-12693
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number42
DOIs
StatePublished - Oct 22 2003
Externally publishedYes

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Enantioselectivity
Aldehydes
Copper
Acetates
X-Rays
X rays
Catalysts
nitroaldol

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Evans, D. A., Seidel, D., Rueping, M., Lam, H. W., Shaw, J. T., & Downey, C. W. (2003). A New Copper Acetate-Bis(oxazoline)-Catalyzed, Enantioselective Henry Reaction. Journal of the American Chemical Society, 125(42), 12692-12693. https://doi.org/10.1021/ja0373871

A New Copper Acetate-Bis(oxazoline)-Catalyzed, Enantioselective Henry Reaction. / Evans, David A.; Seidel, Daniel; Rueping, Magnus; Lam, Hon Wai; Shaw, Jared T.; Downey, C. Wade.

In: Journal of the American Chemical Society, Vol. 125, No. 42, 22.10.2003, p. 12692-12693.

Research output: Contribution to journalArticle

Evans, DA, Seidel, D, Rueping, M, Lam, HW, Shaw, JT & Downey, CW 2003, 'A New Copper Acetate-Bis(oxazoline)-Catalyzed, Enantioselective Henry Reaction', Journal of the American Chemical Society, vol. 125, no. 42, pp. 12692-12693. https://doi.org/10.1021/ja0373871
Evans, David A. ; Seidel, Daniel ; Rueping, Magnus ; Lam, Hon Wai ; Shaw, Jared T. ; Downey, C. Wade. / A New Copper Acetate-Bis(oxazoline)-Catalyzed, Enantioselective Henry Reaction. In: Journal of the American Chemical Society. 2003 ; Vol. 125, No. 42. pp. 12692-12693.
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